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Sid can most often be found around Rathskeller ForkSaloon and Thieves' Landing, frequently loitering inside the saloon and around the brothel. He can also be encountered at the Tumbleweedgang hideout, though he will be hostile. Sid can also be seen doing odd jobs in Thieves' Landing. Sid can also be seen during numerous random encounters, in which he will rob a store or civilian. Marston has the choice of capturing him, killing him, or letting him get away. Winkler also makes a brief appearance during the mission "On Shaky's Ground", in which he can be seen with a prostitute in the brothel. He can also be seen in Tall Trees having a camp together with another criminal. Sid and his companion will either ignore Marston or shoot on sight. Sid can also be seen in Nightwatch job in Blackwater, he is usually a horse thief or a burglar.